Patent GB-479122-A (GB)
Title: Manufacture of esters
IPC: C11D1/12
Filed: 1936-06-24
Abstract: Compounds having the formula (R1)nAX wherein R1 is an aliphatic or cycloaliphatic radicle having at least 3 carbon atoms, n is a whole number, A is an isocyclic radicle and X is COOR2Y, OR3COOR2Y or R3COOR2Y (R2 being an aliphatic or isocyclic radicle, R3 being an aliphatic radicle, the chain of which may be interrupted by hetero atoms and Y being a sulphonic acid or sulphuric ester group) are prepared by condensing, in the form of its acid chloride, the alkylated or cycloalkylated isocyclic carboxylic acid with a hydroxylated aliphatic or isocyclic sulphonic acid or a sulphuric ester thereof or a sulphuric ester of a polyhydroxyaliphatic or isocyclic compound.  The condensation of oxyalkylsulphonic acids or their salts with the compounds having the following formula however is excluded: (R4)n+1 BZCOCl wherein R4 is an aliphatic radicle having at least 3 carbon atoms, n is a whole number, B is an aromatic ring system and Z is an aliphatic hydrocarbon radicle directly linked to B. In a modification an alkali metal salt of the alkylated or cycloalkylated isocyclic carboxylic acid is condensed with a halogenated aliphatic or isocyclic sulphonic acid or sulphuric acid ester or salt thereof.  The products may be used as wetting, foaming, fulling, kier boiling, washing, and dispersing agents. They may be used with other assistants such as pyrophosphate, oxygen yielding substances and stabilizing agents.  Their use for washing wool and as hair washes is also mentioned.  In examples: (1) isooctylphenoxyacetic acid chloride is condensed with the sodium salt of hydroxy ethanesulphonic acid; in order to prepare a washing agent, the product may be mixed with water glass, calcined sodium pyrophosphate, sodium perborate, magnesium sulphate, sodium carbonate and sodium sulphate: (2) isododecylphenoxyacetic acid chloride is condensed with the anhydrous sodium salt of phenolsulphonic acid; the product may be mixed with water glass, sodium pyrophosphate, sodium perborate, magnesium sulphate, sodium carbonate, sodium sulphate and a dodecylphenol-ethyleneoxide reaction product: (3) dibutylphenoxyacetic acid chloride is condensed with sodium hydroxyethane sulphonate: (4) p-dodecylbenzoic acid chloride is condensed with potassium hydroxyethanesulphonate; the product is a levelling and through-dyeing agent: (5) butyl cyclohexylbutyric acid chloride is condensed with sodium hydroxypropanesulphonate: (6) 1 : 6-hydroxyhexanesulphonate is condensed with the perhydrogenated derivative of the acid obtained by condensing phthalic anhydride with benzene: (7) sodium cyclohexanolsulphonate is condensed in the presence of pyridine with isooctylphenylacetic acid chloride: (8) ethionic acid is condensed with tetradecylphenoxyacetic acid: (9) sodium hydroxy ethanesulphonate is condensed with the perhydrogenated derivative of the acid chloride obtained by treating with phosphorus trichloride the condensation product of naphthalene and phthalic anhydride.  isoPropylbenzoic, butylbenzoic, perhydronaphthoic, butylphthalic, dodecylphenylacetic, and triisobutyl hydrocinnamic acids are mentioned as well as the following hydroxy sulphonic and sulphuric esters; 2 : 3-dihydroxypropanesulphonic acid, hydroxybutanedisulphonic acid, cellulose-sulphuric acid esters, glycerine monosulphuric acid esters, cyclohexanol sulphonic acids, hydroxyethyloxyethanesulphonic acid, and carbylsulphate.  The corresponding compounds in which one hydroxy group is exchanged for halogen are also mentioned.  1 : 6-Hydroxyhexanesulphonic acid is obtainable by monoesterifying 1 : 6-hexanediol with hydrochloric acid and reacting the product with sodium sulphite.  iso-Octylphenylacetic acid is obtainable by condensation of di-isobutylene with phenylacetic acid.  Specifications 449,865 and 455,379 are referred to.ALSO:Compounds having the formula (R1)nAX wherein R1 is an aliphatic or cycloaliphatic radicle having at least 3 carbon atoms, n is a whole number, A is an isocyclic radicle and X is COOR2Y, OR3COOR2Y or R3COOR2Y (R2 being an aliphatic or isocyclic radicle, R3 being an aliphatic radicle, the chain of which may be interrupted by other atoms and Y being a sulphonic acid or sulphuric ester group) are prepared by condensing, in the form of its acid chloride, the alkylated or cycloalkylated isocyclic carboxylic acid with a hydroxylated aliphatic or isocyclic sulphonic acid or a sulphuric ester thereof, or a sulphuric ester of a polyhydroxyaliphatic or isocyclic compound.  The condensation of oxyalkylsulphonic acids or their salts with the compounds having the following formula however is excluded: (R4)n + 1 BZCOC1 wherein R4 is an aliphatic radicle having at least 3 carbon atoms, n is a whole number, B is an aromatic ring system and Z is an aliphatic hydrocarbon radicle directly linked to B.  In a modification, an alkali metal salt of the alkylated or cycloalkylated isocyclic carboxylic acid is condensed with a halogenated aliphatic or isocyclic sulphonic acid or sulphuric acid ester or salt thereof. The products may be used as dispersing agents. They may be used with other assistants such as pyrophosphate, oxygen yielding substances and stabilizing agents.  In examples: (1) isooctylphenoxyacetic acid chloride is condensed with the sodium salt of hydroxy ethanesulphonic acid; (2) isododecylphenoxyacetic acid chloride is condensed with the anhydrous sodium salt of phenolsulphonic acid; (3) dibutylphenoxyacetic acid chloride is condensed with sodium hydroxyethane sulphonate; (4) p-dodecylbenzoic acid chloride is condensed with potassium hydroxyethanesulphonate; (5) butylcyclohexylbutyric acid chloride is condensed with sodium hydroxypropanesulphonate; (6) 1 : 6-hydroxyhexanesulphonate is condensed with the perhydrogenated derivative of the acid obtained by condensing phthalic anhydride with benzene; (7) sodium cyclohexanolsulphonate is condensed with isooctylphenylacetic acid chloride; (8) ethionic acid is condensed with tetradecylphenoxyacetic acid; (9) sodium hydroxy ethanesulphonate is condensed with the perhydrogenated derivative of the acid chloride obtained by treating with phosphorus trichloride the condensation product of naphthalene and phthalic anhydride, iso-Propylbenzoic, butylbenzoic, perhydronaphthoic, butylphthalic, dodecylphenylacetic, and triisobutyl hydrocinnamic acids are mentioned as well as the following hydroxy sulphonic and sulphuric esters, 2 : 3-dihydroxypropanesulphonic acid, hydroxybutanedisulphonic acid, cellulosesulphuric acid esters, glycerine monosulphuric acid esters, cyclohexanol sulphonic acids, hydroxyethyloxyethanesulphonic acid, and carbylsulphate. The corresponding compounds in which one hydroxy group is exchanged for halogen are also mentioned.